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The day I cried outside the office
When I first launched my business, I wanted sales, I wanted my business to be successful and I wanted it so badly. I had a list of prospects, a phone in my hand, and a plan. Make the calls. Set the meetings. Win the work.
The home office was set up. I sat their with my script and my best intentions. My chest tightened, my inner dialogue spiralled and I felt panicked. I couldn’t do it. I ran out out of the office and sat outside crying because in that moment I believed sales calls were the only way to succeed and I was too scared to make them.
I felt humiliated, I wanted to provide for myself, for my wife, I wanted to set ourselves up but I was stuck. I wanted the ground to swallow me.
That was the day I realised something important about fear. It is not logical. It does not care about your goals. It shows up to keep you “safe” and small. And if you let it, it will run your life.
The universe is annoying like that
Have you noticed how the thing you most need to do is often the thing you least want to do?
It is like the universe puts the biggest growth, the biggest rewards, behind the most uncomfortable door.
Make the call. Ask for the raise. Invest your first thousand into a global index fund!

Walk across the room and talk to the attractive human you can’t stop thinking about.
The uncomfortable door is the one with your brightest future behind it. The universe is annoying like that, but it is also generous. Open the door and it rewards you with learning, momentum, and pride.
I was that shy kid under the table
I didn’t start brave. As a kid I would go bright red speaking to strangers. Hot face. Sweaty palms. Total shutdown.
I remember being at a Chinese restaurant with my dad. There was a piano player taking requests. Dad handed me tip money and told me to go ask for a song.
I could not do it. The more my dad tried to encourage / force me to do it the worse the social anxiety became. I hid under the table, mortified. I felt so small and so visible at the same time. That red face panic stayed with me for years.
The three‑second rule that saved me
Even now I get weird about making phone calls. I can put them off while my brain makes me think about how uncomfortable this is going to be!
The tool that consistently works for me is the three‑second rule. If I know the next right action, I give myself three seconds to start it before my brain talks me out of it.
Just do it before you can think!

- Three. Two. One. Dial.
- Three. Two. One. Hit publish.
- Three. Two. One. Walk over and say hello.
Action first. Explanations later. Move within three seconds and fear does not get the wheel.
Discomfort is the doorway
Did you know that Katie and I started a band with our friend Finn? We called ourselves the Rebelutionaries and wrote an entire album called Money Revolution all about index funds, money and financial freedom.
Our new single “Discomfort” is not about pain for pain’s sake. It is about choosing the stretch activity, because everything you want is on the other side of discomfort. The chorus captures it:
Everything you want is outside your comfort zone,
Break the mould, dare to embrace the unknown.
Get excited to face your deepest fears,
The fear you embrace is your strength.
🎧 Listen to “Discomfort” now:

Why I wrote this song
I wrote “Discomfort” because I wanted to scream to the world: do what makes you uncomfortable. That is where the magic is.
One of my biggest regrets? I did not approach the gorgeous girl I liked. I was too shy. I didn’t take the opportunity to speak at an event that was laid in front of me, I was too nervous. I did not make the calls when I started my business. The pain that caused me was huge.
Avoid my regret. Avoid the pain. Play the song. Take action. The universe will not make it easy, but it will make it worth it.
The first‑time fallacy
The first time you do anything it feels weird and uncomfortable. People use that feeling as proof it is not for them.
“I tried it once and it felt wrong.”
I want to scream “Of course it did. First times are awkward by design!”
The first time I spoke in public I was so nervous, sweaty and uncomfortable. I kept going. I joined Toastmasters. It gave me a safe place to practise and get feedback. Awkward turned into fun. Fear turned into skill.

Speaking in front of an audience, inspiring people, making people laugh became one of the things I love to do the most. It has created immense joy in my life and others. All because I didn’t give up when it felt awkward!
Even after years of public speaking trying Stand Up Comedy for the first time felt SUPER uncomfortable again! Image 100 drunk people starring at you thinking “Come on then funny boy, make me laugh!”
With enough reps you change your identity from “I am scared” to “I am someone who does the thing.”
Three ideas that keep me moving
- Discomfort is information, not a stop sign. It points to where growth lives. It tells me where to go next.
- Action shrinks fear. The three‑second rule turns mountains into hills. If you take action, most of the time you think afterwards “That wasn’t too bad!”
- Reps change identity. With enough practice you become the kind of person who acts.
Tiny action today
Pick one uncomfortable door. The call. The conversation. The email. The gym. The investment account. Count down from three and start. Do not wait for courage to arrive. Courage is waiting on the other side of action for you.
Listen to the full Money Revolution album
Money Revolution — the world’s first financial independence music album. 21 tracks. Zero record labels. 100% rebel‑approved.
Songs about investing, compounding and breaking free from the rat race.
🎧 Stream the full album here:

Are you ready to step into discomfort?
I would love to know what you think of the song, the album or what action you have taken to improve your life after this blog post.
The pain of regret is 10 times the pain of discomfort and it lasts a lot longer! Take action now!
Peace and Pineapples
Alan, Katie and Finn
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Brilliant article, Alan.
I especially love the three ideas that keep you moving – discomfort is information, action shrinks fear, reps change identity.
Absolutely true. What a great reminder. Thank you.
Move over Bad Omens – here come the Rebelutionaries!
Tanya! Happy New year. Sending you happiness. Alan